Base induced chiral substituted furans and imidazoles from carbohydrate-derived 2-haloenones

Kanchan Mal, Indrajit Das

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Chiral substituted furans and imidazoles are key intermediates to access biologically important molecules. We describe herein a catalyst/ligand free cascade Michael-type addition/intramolecular cyclization/carbohydrate-ring opening of 2-haloenones with 1,3-dicarbonyl compounds or amidines utilizing K2CO3/DMSO at ambient temperature that provides a straightforward approach to a variety of optically active (poly)hydroxy furans and imidazoles containing multiple stereocenters with good yield and excellent regioselectivity. The furan intermediates provide efficient access to synthetically valuable substituted α-benzyloxyvinyl ketones. The NMR spectrum of the substituted 2-methylfurans shows an unusual long-range (5JH-H) 1H-1H COSY cross-peak between C2-CH3 and C4-H signals.

Original languageEnglish
Pages (from-to)932-945
Number of pages14
JournalJournal of Organic Chemistry
Volume81
Issue number3
DOIs
StatePublished - 5 Feb 2016
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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